7 Messiest Bachelor Nation Splits: Colton & Cassie, Andi & Josh & More

You win some, you lose some. While 'The Bachelor' and its many spinoffs have produced successful relationships, and even marriages, not all who compete on the reality dating show have been so lucky.

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Image Credit: XPX/STAR MAX/IPx

Not all relationships have a fairytale ending, and nobody knows that better than these Bachelor Nation contestants. Amid reports that Cassie Randolph, 25, has filed for a restraining order against her former beau Colton Underwood, 28, we’re looking back at some of the messiest splits between couples on The Bachelor and The Bachelorette. Who could forget the fiasco that took place earlier this year when Peter Weber aka Pilot Pete managed to break not one, but two hearts at the conclusion of his season, or the extremely messy break up between Jordan Kimball and Jenna Cooper after Bachelor In Paradise. Here are 7 of the worst Bachie splits.

Colton & Cassie
The Bachelor’s Colton and Cassie had a messy split. Image: XPX/STAR MAX/IPx
Cassie and Colton met on Season 23 of The Bachelor, which aired in early 2019. Producers teased an ending that had never been seen before in Bachelor history, and they certainly served the drama when Cassie left the show, and Colton dumped Tayshia Adams and Hannah Godwin to pursue Cassie. There were no signs of trouble in paradise until the pair decided to go their separate ways in May, totally taking Bachelor Nation by surprise. Shortly after, Cassie called Colton out for allegedly sharing intimate details about their relationship with the public, and on September 11, TMZ reported that she filed for a restraining order at a Los Angeles court.
Andi & Josh Murray
Andi & Josh Murray. Image: RW/MediaPunch/IPx
Fan-favorite Andi Dorfman was the Season 10 Bachelorette, and she became engaged to Josh Murray when she accepted his proposal on the finale of the reality dating show in 2014. Nevertheless, the pair split in 2015, saying in a joint statement, “After several months of being engaged and working on our relationship, we have decided that it’s best for both of us to go our separate ways. We are very sad that it has come to this point, but this is what’s best for both of us individually.” Of course, Bachelor fans would know that Josh went on to appear in a Bachelor spin-off show…
Josh Murray & Amanda Stanton
Josh & Amanda. Image: Sipa USA via AP
After his split from Andi, Josh went on to appear on the third season of Bachelor in Paradise, where he met and became engaged to Amanda Stanton in 2016. Yep, just one year after he and Andi broke off their engagement. The pair split just a few months later in January 2017. Amanda, who previously appeared on Ben Higgins‘ season of The Bachelor opened up in her 2019 memoir about Josh’s “controlling” behavior. “If he doesn’t turn into your prince, stop kissing him. Josh’s behavior was very frog like. There were control issues, more than a few untruths told, plus other red flags along the way … I kept kissing him hoping he’d turn into a prince,” she wrote in her book. “I knew Josh was kind of controlling. I knew Josh was controlling when we were filming, but the second we got home from the show, he went full throttle.”
Jake Pavelka & Vienna
Jake & Vienna. Image: AP Images
Flash back one decade, and Jake Pavelka was our Bachelor. He proposed to Vienna Girardi on the show’s season finale but the pair announced their split just a few months later, in June 2010. She reportedly returned the three-carat diamond engagement ring he gave her, and Jake went on to accuse her of being unfaithful (which she denied). Jake gave an interview to Access Hollywood Live the following year, and alleged that Vienna had her publicist call him to end the engagement. “I got a call from her publicist saying Vienna has sold your break up story to Star Magazine and your relationship is over,” he claimed.
Jenna Cooper & Jordan Kimball 
Jenna & Jordan. Image: ABC/Paul Hebert
Jordan Kimball and Jenna Cooper got engaged on the finale of Bachelor in Paradise‘s fifth season, which aired on Sept. 11, 2018. Just one day later, Jordan revealed that they had split, after text messages that were allegedly exchanged between Jenna and an unknown man were leaked. After Jordan implied that Jenna had cheated, her lawyer accused Jordan of fabricating the texts. Her attorney threatened legal action against him if he did not come out publicly and say that he knew the texts were fabricated. Reality Steve, the popular website which posted the initial story, then retracted the claims made about Jenna and called the reporting the “biggest misstep” of his career.
Peter Weber & Madison / Hannah Ann
Peter with Hannah Ann. Image: ABC
Ah, who could forget the mess that was Pilot Pete’s season! In the two-part finale, winner Hannah Ann Sluss (who Peter subsequently broke up with) came completely prepared to let him know exactly how she felt following their split. Hannah completely told Peter off for “taking away [her] first engagement” and urged him to “become a real man” if he really wants to be with someone in the future. Following Hannah Ann and Peter’s breakup, it seemed like Peter and his runner-up, Madison Prewett, were going to give their relationship another shot, after Madison memorably left Peter in Australia then returned to LA following his split from Hannah Ann. But only days after the live finale, Madison and Peter called it quits. Yikes.
Courtney Robertson & Ben Flajnik
Courtney & Ben. Image: Ziegler/McMullan/Sipa Press
After nearly eight months of dating, the Bachelor couple, who got engaged in 2012, called it quitsciting distance as one of many factors. “After meeting over a year ago, we have decided to end our romantic relationship. The ups and downs weighed heavily on us both and ultimately we started to grow apart because of the distance, time apart, and our need to focus on our respective careers,” the couple said in a joint statement. “We have nothing but the utmost respect for each other … thanks to everyone for your love and support, it’s been quite a ride.” Courtney was later spotted returning her engagement ring, but shortly after she was spotted smooching fellow Bachelor Nation contestant Arie Luyendyk Jr​..